$0
for 0 nights

Home in Anna Maria, Florida

5 bedrooms

0 beds

5 bathrooms

8 guests

1000 sq. ft.

Luxury

Elevated properties with standout design

Operated by a Wander partner

Trusted operators, vetted by Wander

About the property

Welcome to Cloud 9, a stunning beachfront retreat where modern luxury meets relaxed coastal living. Perfectly positioned on the quiet north end of Anna Maria Island, this beautifully designed 5-bedroom home offers everything your group needs for an unforgettable island escape — from elegant interiors to effortless beach access just moments away. Experience luxury in our five-bedroom home, meticulously designed for comfort and enjoyment. Each of the four king suites is a sanctuary, featuring a private en-suite bathroom and a TV for your entertainment. The bunk room offers a fun and flexible space with full-over-full bunk beds, perfect for kids or additional guests. A convenient half bath is located just outside the bunk room. The gourmet chef's kitchen is equipped with a 48-inch gas range, ideal for preparing delicious meals. Enjoy outdoor dining with the gas BBQ on the pool deck. Unwind on the private covered porch with a wine cooler, offering stunning Gulf sunset views. This property provides easy beach access and is a short walk to Bean Point. The pool deck is perfect for grilling, lounging, and socializing. Guests have access to adult bikes, paddle boards, and a kayak for exploring the area. A complimentary 6-passenger street-legal golf cart is also provided for easy island navigation. Cloud 9 is ideally situated on Anna Maria Island's walkable North End, offering easy access to the beach, Bean Point, and the shops and restaurants of Pine Avenue. For exploring further, the free island trolley provides convenient transportation, with a stop located right on Pine Ave. Free parking is available on the premises and on the street. The closest major airport is approximately a 1-hour drive away. Please review and agree to the Reservation Agreement. Rates and Availability are subject to change until reservation is completed. A deposit must be received in order to reserve the dates you desire. Pets- Non-Aggressive breeds, vaccinated & current on a flea prevention program allowed only with prior approval. Pet Fee and Pet Waiver Required. $300 per pet Any unauthorized pets= 25% surcharge Traveler must provide photo ID and guest list If for some reason the property you booked is unavailable, we may offer to rebook the Traveler at another property, if a substantially similar property is available for the same period and under a new reservation. Owner is not responsible for events beyond our control, ie: inclement weather, storms, evacuations, etc. Travel Insurance is recommended and may be purchased independently from several sites (Red Sky Travel Insurance, Square Mouth, etc.) Due to the extensive equipment provided at the home, there are additional documents required. The use of the bikes, SUP and Kayak require a signed Equipment Waiver for anyone 18+ All Drivers of the property's Golf Cart must be 25, and provide a copy of a valid U.S. Driver's License and Insurance.

Where you’ll sleep

Bedroom 1

1 king bed

Bedroom 2

1 king bed

Bedroom 3

1 king bed

Bedroom 4

1 king bed

Bunk Bedroom

1 twin bunk bed

Bedroom 1

1 king bed

Bedroom 2

1 king bed

Bedroom 3

1 king bed

Bedroom 4

1 king bed

Bunk Bedroom

1 twin bunk bed

Amenities

Common Amenities

  • Sound system
  • Beach essentials
  • Long term stays allowed
  • Elevator
  • Wifi
  • Garage
  • Luggage drop off allowed
  • Free parking
  • Beachfront
  • Bicycle
  • Wine Cellar
  • Pet relief area
  • Balcony
  • Water slide
  • Hike trail nearby
  • Boat
  • Bay views
  • Private Chef
  • Fishing Area
  • Golf Course
  • Beach access
  • Hot water
  • Fire extinguisher
  • Air conditioning
  • Smoke detector
  • First aid kit
  • Kitchen
  • Fire place
  • Heating
  • Iron
  • Patio
  • Waterfront
  • Ocean view
  • Carbon monoxide detector
  • Hangers
  • Dedicated workspace
  • Crib
  • Garden
  • High chair
  • Extra pillows
  • Ice maker
  • Stair gate
  • Board games
  • Baking sheet
  • Mini fridge
  • Safe
  • Toys
  • Closet
  • Beach
  • Beach View
  • Children’s dinnerware
  • Cleaning Disinfection
  • Cleaning products
  • Enhanced cleaning practices
  • Essentials
  • Family/kid friendly
  • Fishing
  • Golf - Optional
  • High touch surfaces disinfected
  • Horseback Riding
  • Pets allowed
  • Private entrance
  • Shopping
  • Spa
  • Suitable for children (2-12 years)
  • Suitable for events
  • Suitable for infants (under 2 years)
  • Water Sports
  • Water View
  • Gym
  • Tennis court
  • Children dinnerware
  • Pack n play
  • Books
  • Basketball Court
  • Massage table
  • Heated pool
  • Laundromat nearby
  • Ironing board
  • Bedroom door lock

Pool

  • Outdoor pool
  • Hot tub

Patio

  • Outdoor seating
  • Outdoor dining area
  • Ceiling fan
  • TV
  • BBQ Area
  • BBQ Utensils
  • Paddle board
  • Kayaks
  • Cornhole

Balcony 1

  • Outdoor seating

Balcony 2

  • Outdoor seating

Living Room

  • TV

Dining Room

  • Dining table

Kitchen

  • Cooking basics
  • Coffee
  • Blender
  • Coffee maker
  • Dishwasher
  • Fridge
  • Kettle
  • Microwave
  • Freezer
  • Oven
  • Pots and pans
  • Spices
  • Stove
  • Tea
  • Toaster
  • Wine glasses
  • Dishes
  • Silverware

Common Area

  • Coffee maker
  • Coffee
  • Kitchenette

Bedroom 1

  • Bed linens

Ensuite Bathroom 1

  • Bath linens
  • Ensuite bathroom
  • Body soap
  • Shampoo
  • Shower gel
  • Shower
  • Conditioner
  • Toilet
  • Hair dryer
  • Bathtub

Bedroom 2

  • TV
  • Bed linens

Ensuite Bathroom 2

  • Bath linens
  • Body soap
  • Ensuite bathroom
  • Shampoo
  • Conditioner
  • Shower
  • Shower gel
  • Toilet

Bedroom 3

  • Bed linens
  • TV

Ensuite Bathroom 3

  • Bath linens
  • Body soap
  • Shampoo
  • Conditioner
  • Shower
  • Shower gel
  • Ensuite bathroom
  • Toilet

Bedroom 4

  • TV
  • Bed linens

Ensuite Bathroom 4

  • Bath linens
  • Ensuite bathroom
  • Body soap
  • Shampoo
  • Conditioner
  • Shower
  • Shower gel
  • Toilet

Bunk Bedroom

  • Bed linens
  • TV
  • Ceiling fan

Ensuite Bathroom 5

  • Ensuite bathroom
  • Bath linens
  • Toilet
  • Body soap

Half Bath 1

  • Bath linens
  • Body soap
  • Half bath
  • Toilet

Half Bath 2

  • Bath linens
  • Half bath
  • Toilet
  • Body soap

Laundry Room

  • Washer
  • Dryer
  • Cleaning supplies

4.9 · 77 reviews

Where you’ll be

Anna Maria, Florida 34216, US

Anna Maria, Florida, US
27.53618622-82.73771667
Timezone: America/New_York

Restaurants

Hurricane Hanks

Hurricane Hanks offers fresh, high-quality American and seafood dishes in a casual, laid-back atmosphere perfect for families and sports fans alike. Enjoy flavorful burgers, seafood specialties, and strong cocktails in the heart of Holmes Beach.

Anna Maria Island Beach Cafe

Anna Maria Island Beach Cafe offers casual dining with stunning Gulf views, featuring all-you-can-eat pancakes and seafood specials. Enjoy live music and "Island Size" drinks at the Bamboo Beach Bar.

The Ugly Grouper

The Ugly Grouper offers a lively dining experience with fresh seafood and American cuisine, complemented by live music and outdoor seating. Its fun atmosphere includes games and a full bar, making it a great spot for family and friends.

Sandbar Seafood + Spirits

Sandbar Seafood + Spirits offers fresh, locally sourced seafood and vibrant farm-to-fork dishes in a relaxed beachfront setting where you can dine with your toes in the sand while enjoying stunning Gulf Coast sunsets.

The Waterfront Restaurant

The Waterfront Restaurant offers fresh seafood and classic American dishes in a cozy, laid-back atmosphere, complemented by its stunning waterfront location. It also features a "catch and cook" option, where they prepare your freshly caught fish.

Compass Hotel Anna Maria Sound by Margaritaville

Enjoy fresh seafood and steak at Compass Hotel's Floridays, a waterfront eatery inspired by classic Florida fish houses. The hotel also offers signature Margaritaville drinks at Compass Bar & Chill, perfect for a relaxing getaway.

The Porch Restaurant Anna Maria

The Porch Restaurant offers a refined dining experience with top-quality steak, fresh fish, and seasonal entrées, set within a historic home on Anna Maria Island. Its intimate ambiance and extensive wine selection make it a sought-after destination.

Skinny's Place inc.

Skinny's Place is a classic beachside eatery offering juicy burgers and crispy fries in a casual, laid-back atmosphere. This island staple has been serving up Old Florida charm since 1952.

Ginny's & Jane E's Cafe and Gift Store

Ginny's & Jane E's Cafe offers a blend of classic and seasonal dishes in a cozy setting, complemented by a unique gift store featuring local art and beachwear. The cafe's warm ambiance reflects "Old Florida" hospitality.

Rod and Reel Pier

Rod and Reel Pier offers a relaxed dining experience with fresh seafood and stunning views of Tampa Bay. Its quaint atmosphere and historic charm make it a beloved spot for both locals and visitors.

Attractions

Fort De Soto Park Batteries And Military Post

Explore Fort De Soto Park's historic batteries and military post, featuring the last four surviving 12-inch seacoast mortars in the continental U.S. History buffs and nature lovers alike will enjoy this unique blend of military history and scenic Gulf views.

Beach N Rides

A trusted local provider to ensure you have easy access to high-quality golf cart rentals during your stay. You may contact Beach N Rides at 941-251-7916. Use the discount code: Serendipity at checkout to receive your special rate.

Coconut Rentals

A trusted local provider to ensure you have easy access to high-quality golf cart rentals during your stay. You may contact Coconut Rentals at 941-269-1080. Use the discount code: Serendipity at checkout to receive your special rate.

Ana Maria island

Explore Anna Maria Island's serene waters by paddleboarding or kayaking, perfect for beginners and nature lovers alike. Enjoy the peaceful scenery and wildlife amidst the island's mangroves.

Manatee Public Beach

Manatee Public Beach offers a serene escape with pristine white sands and tranquil waters, perfect for those seeking relaxation and fun activities like swimming and paddleboarding. It's ideal for families and beach lovers alike.

Anna Maria Island Beach

Anna Maria Island Beach offers serene white sands and clear waters, perfect for families and couples seeking a tranquil beach experience with opportunities for snorkeling, shelling, and sunset walks. It's ideal for those looking for a peaceful and scenic getaway.

De Soto National Memorial

Explore De Soto National Memorial, where history meets nature. This tranquil park offers hiking, kayaking, and living history programs, perfect for nature lovers and history enthusiasts alike.

Robinson Preserve

Explore Robinson Preserve's unique blend of nature and adventure, featuring hiking trails, kayaking, and mangrove forests, perfect for outdoor enthusiasts and families. This 500-acre haven offers a serene escape from crowded beaches, ideal for those seeking a tranquil yet active experience.

Fort De Soto Dog Park / Beach

Fort De Soto Dog Park and Beach offers a unique experience where dogs can play off-leash and swim, making it perfect for dog owners. The park's large fenced areas and beach access provide ample space for socialization and fun.

Holmes Beach

Holmes Beach offers a serene getaway with activities like paddleboarding and boat tours, perfect for those seeking a relaxed beach experience. It's ideal for families and adventure-seekers alike, providing a mix of leisure and exploration.

Bean Point Beach Access

Enjoy a serene beach experience at Bean Point, where tranquil surroundings and stunning coastal views make it perfect for nature seekers and those seeking solitude. It's ideal for beachcombers and surf fishing enthusiasts alike.

Palma Sola Botanical Park

Palma Sola Botanical Park offers a serene escape with its diverse tropical and temperate species, perfect for nature lovers and families. The park's unique Rare Fruit Trail and beautiful gardens make it a special destination for those seeking tranquility and botanical exploration.

Things to know

Cancellation policy

Free cancellation up to 14 days before check-in. 50% refund up to 7 days before. No refund after that.

Property rules

Pets allowed with fee

No smoking - fees will apply

Events allowed

Safety & security

Check-in after 4:00 pm

Check-out before 10:00 am

8 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
May 31, 2026$1558Not Available
Jun 1, 2026$1773Not Available
Jun 2, 2026$1415Not Available
Jun 3, 2026$1409Not Available
Jun 4, 2026$1406Not Available
Jun 5, 2026$2021Not Available
Jun 6, 2026$2002Not Available
Jun 7, 2026$1514Not Available
Jun 8, 2026$1517Not Available
Jun 9, 2026$1381Not Available
Jun 10, 2026$1371Not Available
Jun 11, 2026$1402Not Available
Jun 12, 2026$2054Not Available
Jun 13, 2026$2055Not Available
Jun 14, 2026$1563Not Available
Jun 15, 2026$1571Not Available
Jun 16, 2026$1444Not Available
Jun 17, 2026$1604Not Available
Jun 18, 2026$1966Not Available
Jun 19, 2026$2795Not Available
Jun 20, 2026$2782Not Available
Jun 21, 2026$1789Not Available
Jun 22, 2026$1820Not Available
Jun 23, 2026$1665Not Available
Jun 24, 2026$1683Not Available
Jun 25, 2026$1703Not Available
Jun 26, 2026$2544Not Available
Jun 27, 2026$2548Available
Jun 28, 2026$1929Available
Jun 29, 2026$1950Not Available
Jun 30, 2026$1790Not Available
Jul 1, 2026$2099Not Available
Jul 2, 2026$2455Not Available
Jul 3, 2026$3468Not Available
Jul 4, 2026$3868Not Available
Jul 5, 2026$3275Not Available
Jul 6, 2026$2212Not Available
Jul 7, 2026$2021Not Available
Jul 8, 2026$2020Not Available
Jul 9, 2026$2029Not Available
Jul 10, 2026$2817Not Available
Jul 11, 2026$2799Not Available
Jul 12, 2026$2183Not Available
Jul 13, 2026$2175Not Available
Jul 14, 2026$2006Not Available
Jul 15, 2026$2012Not Available
Jul 16, 2026$2026Not Available
Jul 17, 2026$2826Not Available
Jul 18, 2026$2818Not Available
Jul 19, 2026$2197Available
Jul 20, 2026$2183Available
Jul 21, 2026$2026Available
Jul 22, 2026$2049Available
Jul 23, 2026$2066Not Available
Jul 24, 2026$2864Not Available
Jul 25, 2026$2866Not Available
Jul 26, 2026$2263Not Available
Jul 27, 2026$2248Not Available
Jul 28, 2026$2066Not Available
Jul 29, 2026$2064Not Available
Jul 30, 2026$2069Not Available
Jul 31, 2026$2846Not Available
Aug 1, 2026$2180Not Available
Aug 2, 2026$1536Not Available
Aug 3, 2026$1501Not Available
Aug 4, 2026$1300Not Available
Aug 5, 2026$1255Not Available
Aug 6, 2026$1205Not Available
Aug 7, 2026$1960Not Available
Aug 8, 2026$1940Not Available
Aug 9, 2026$1317Not Available
Aug 10, 2026$1275Not Available
Aug 11, 2026$1200Not Available
Aug 12, 2026$1200Not Available
Aug 13, 2026$1200Not Available
Aug 14, 2026$1780Not Available
Aug 15, 2026$1770Not Available
Aug 16, 2026$1200Not Available
Aug 17, 2026$1200Not Available
Aug 18, 2026$1200Not Available
Aug 19, 2026$1200Not Available
Aug 20, 2026$1200Not Available
Aug 21, 2026$1720Not Available
Aug 22, 2026$1739Not Available
Aug 23, 2026$1800Available
Aug 24, 2026$1800Available
Aug 25, 2026$1800Available
Aug 26, 2026$1800Available
Aug 27, 2026$1800Available
Aug 28, 2026$1800Available
Aug 29, 2026$1800Available